


wagered

by WattStalf



Series: Commissions [400]
Category: Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Black & White | Pokemon Black and White Versions, Pocket Monsters: FireRed & LeafGreen | Pokemon FireRed & LeafGreen Versions
Genre: 69 (Sex Position), Blow Jobs, Cunnilingus, F/M, Shotacon, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2021-03-03
Updated: 2021-03-03
Packaged: 2021-03-16 17:09:18
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 5,022
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29828205
Author URL: https://archiveofourown.org/users/WattStalf/pseuds/WattStalf
Summary: Red has a habit of making wagers with older trainers, and Skyla is excited to talk advantage of that.
Relationships: Huuro | Skyla/Red
Series: Commissions [400]
Series URL: https://archiveofourown.org/series/1325462
Comments: 1
Kudos: 4





	wagered

Red is a promising young trainer who has developed quite the strange habit in his travels throughout other regions. After leaving his hometown, he traveled all over Kanto, making a name for himself despite being so young, and now, he is well-known wherever he goes, often getting into battles with other strong trainers along the way. However, he has a habit of letting certain types of trainers make specific wagers with him; his trainer of choice is an older woman, and it seems that there are more than a few girls older than him, that would love to have a chance with a cute boy like him.

In Unova, he challenges Skyla, who is excited to make that sort of bet with him, and excited to give it her all. It might be a little unfair, but that is his own choice. He knows that she is a Flying type specialist, and yet the team he brings with him does not allow him many good chances to get an advantage over her. It only makes sense that he loses, and once their battle is concluded, Skyla is very eager to claim her prize.

“So, we get to do whatever I want, right?” she asks. Red, a soft spoken boy, simply nods. “Then let’s go ahead and get these clothes off, alright?” With that, she starts to strip down, and Red does as well, knowing this game well enough, and just as eager to get started as she is. Once both of them are naked, she says that she has a few ideas for what she wants to do with him, and Red looks forward to doing everything that she wants.

“And someday, we should have a rematch,” she goes on to say, “so that you can show me what you’re _really_ made of.” Red understands the meaning behind her words; she knows that he did not try as hard as he could, because he wanted to do things her way, and though she is glad to get that chance, she always wants to see him go all out, so that she might get the chance to experience things his way. Next time, he will more than likely be the one in control, but for right now, both of them are excited to get to do what she has in mind.

He is still so young that it is not hard for her to lift him to do things standing. In fact, she is even able to flip him so that, while she holds him in her arms, she is able to suck him off, while his head just reaches between her legs. Red knows exactly what to do here, and she stands with her legs slightly spread, so that he can duck his head between them and start licking along her slit, teasing her as he gets ready. He has gotten a little bit of experience in such things from other trainers, most notably Cynthia, who trained him well in the erotic arts, and so, he hopes that he will be able to properly please Skyla.

But as soon as she wraps her lips around the head of his cock, he forgets everything for a moment, his whimper muffled against her pussy. Red is not particularly loud, but during sex, it can be easy for an older woman to get him to make quite a bit of noise for her, and Skyla is not the first to be curious about just how noisy she can make Red get. She looks forward to hearing him moan for her, and that whimper is just the start of the fun.

For a little while, Red is not able to do much to her, so caught up in his own excitement that he is a little too dazed to keep things going. She does not mind that, willing to let him take however much time he needs to get back into the swing of things, and glad to take her time teasing him with her mouth, drawing him deeper into it, until she has engulfed his entire cock and has started sucking on him.

Red’s muffled whimpers do soon turn into moans, and she really likes the sound of that. He is adorable when he starts to lose himself, seeming that much more like the kid that he is. Normally, he seems so serious for his age, but when he starts to go to pieces like this, while she is able to hold him so easily in his arms, she can’t help but think about how young and cute she is, making him exactly her type. If she could, she would keep this up forever, bobbing her head on his cock, as he struggles to regain his composure so that he can get back to it.

But soon enough, he is able to start licking at her pussy again, even with the way his head is swimming from all of this pleasure. Red is eager to start eating her out, wanting to make her feel good just the same way that she is making him feel good. After all, this is supposed to be her prize for winning the battle, and it is not exactly fair if she ends up having to do all of the work for him. Working his tongue inside of her, he soon has Skyla letting out muffled moans around his cock.

The two of them remain like this, as they both fall into their pattern, with Skyla bobbing her head on his cock while Red teases her with his tongue, delving deeper into her and using the knowledge that he has picked up along the way, the things that he has learned on his journeys. He proves himself to be rather skilled at this by now, and Skyla knows that she is lucky to have happened upon a young boy like him, one that can satisfy her needs like this, sending shivers of pleasure throughout her whole body.

As Red delves deeper into her with his tongue, enjoying the taste he gets for her, he can also feel himself nearing his climax as she sucks him off. He does his best to hold back on that, wanting to make sure that he is able to make her feel just as good first, before he allows himself to give into his pleasure. Though that is hard, he likes to think that he has a little bit of experience with training his endurance, doing everything that he can to make sure that he holds back, not letting himself come too soon, both so that he can enjoy things longer, and so that he can make her feel good, make sure that she enjoys herself.

In the short time that he has been doing things like this, he has learned quite a bit, training himself just as seriously in these matters as he would in anything else. Not only is he a top rate trainer, but he is turning himself into a top rate young lover, the sort of boy that can make most grown women lose their minds with pleasure. And he can’t help himself, can’t help wanting to get better and better at it, now that he knows just how much he loves letting those grown women use him for their own pleasure.

Right now, all of his focus is on eating Skyla out while he tries to ignore how good it feels to have her suck his cock. His body will not hold out much longer, but he can feel her getting tense, and she moans and drools around his cock, so he knows that she must be close as well, must be steadily getting there, so for now, he just wants to keep enduring, keep waiting it out, until he is finally able to get her to the edge.

Skyla can tell that Red is doing his best to hold out until the end, can tell that he is fighting against his need to come so that he can make her feel good as well. So she does not hold back at all, does not try and prolong things, and instead just lets herself get completely swept away in it all, and lets herself come once she feels like she is on the edge. When she holds nothing back like this, she can just give in, her legs barely able to support her as her body is wracked with spasms, pleasure coursing through her. The only reason that she is able to maintain any stability is because she does not want to let go of Red, still supporting his entire weight in her arms.

As soon as Skyla starts coming, that is Red’s cue to not hold back anymore either, and he comes down her throat, whining out as he does, letting her swallow it all down. The two of them take some time to calm down after that, but Skyla is not done with him yet, and still has more of her prize to claim. She wants to keep going with him, just as soon as he is ready for more, and fortunately for both of them, being a young boy, Red has plenty of stamina, so it does not take long for him to bounce back from this.

He is soon ready to go again, and this time, Skyla has him lay on his back so that she can get on top of him. She straddles him, rubbing her pussy against his cock, letting him feel how wet she is, something that he already knows rather well just from eating her out. He loves to know that he has that sort of effect on her, and she loves to show him just how horny a young boy like him can get her. Red really is just her type, and so, after teasing this out for a little while, she is no longer able to resist him, and starts to push down onto him, letting his cock press up into her.

Being penetrated by him is everything that she needs, and she moans for him, so needy and so pathetic, but not nearly as pathetic as the noises that he makes for her while being pushed into her. Her pussy is so tight around his cock, a perfect fit that overwhelms him immediately, making it hard for him to think at all. But he does not need to think right now; he just needs to lay back and let Skyla handle everything.

That is the best part of being the loser; as long as he can keep up with whatever she wants, she is always going to take the lead, to show him what he needs to do and take whatever she wants. She can just use him to her heart’s content, and he knows that he is doing things just right. Though he does enjoy taking charge, right now, he likes to have an older woman use him and take control of him, getting more and more excited, as she takes his cock all the way.

Once he is completely buried inside of her, she starts teasing him again, by slowly rising up and sinking down on his cock. He is left whining out for her, and Skyla smiles down at him, commenting on just how cute he is like this, and how much she loves to fuck him. She loves riding him, loves having his cock inside of her, and loves teaching him just how to properly please her. Both of them are glad that she won this battle, and both are looking forward to the next battle to see what happens, but overall, both are just happy to live in the moment.

Slowly but surely, Skyla does start to pick up the pace, still trying to tease things out for as long as she can, so that she can make sure that it all lasts, that she enjoys it as much as possible. Red is completely helpless underneath her as he is swept away in that pleasure, knowing that he will not be able to last long like this, but once again trying his best to make sure that he lasts as long as possible. Her pussy is so perfectly tight around his cock, and he moans out for her as she falls into a quicker pace, riding him and chasing her orgasm, so excited for him that she can hardly contain herself.

“Good boy, such a good boy,” she coos, praising him happily as she uses his body to her heart’s content. Her prize for her victory is everything that she could ever want, everything that she could ever need, and she is so glad that he decided to try and throw the match, all so that he could let her have her way with him. She is not sure if she would ever be able to beat a trainer of his level on her own, but none of that seems to matter right now, as she bounces on top of his cock, finally letting herself get completely lost in her lust, finally letting herself get so carried away that she can’t bring herself to slow down.

Harder and faster, she lets herself get completely carried away, until she is nearing her orgasm, and of course, she can’t bring herself to slow down then. All she wants to do is keep reaching for another climax, wanting to use Red as much as it takes for her to get there. At the same time, he is fighting against his own climax, trying so hard not to give in, as much as he needs it, as much as his body might be aching for this release. All he can do is hold on, helping Skyla to reach that peak first, and then he can let go with her.

It does not take her much longer, at least, and once she is there, she is left screaming on top of him, writhing as she succumbs to an intense orgasm, and Red can’t hold back then, jerking his hips up until he is right there with her, until the two of them are both lost in the same pleasure. She has claimed her prize, but it seems that this was something perfect for the both of them, with Red not really feeling like a loser at all.

~X~

It is not long before Skyla is ready for the rematch, and this time, Red makes sure to bring a team that he knows is better suited for dealing with her. He knows that winning against her will not be as much of a struggle this time, so he should be able to pull it off. Even if he were to lose, he would not mind doing whatever she wanted a second time, but since she wants to experience things from the other side, and because he already has in mind what he wants to do to her, he is not going to hold anything back, determined to secure victory for himself.

And when it comes time for the big battle, the two of them face off together, with Red calling out his first Pokemon, so that things can finally get underway. Victory comes to him about as easily as he expects it to, and he is excited when her last Pokemon goes down. He can see the way she is squeezing her thighs together, trying to keep her arousal in check, and she must have been thinking about it throughout the whole battle, eager to have another round with him.

“Now you get to do whatever you want to me, right?” she asks, the excitement clear in her voice. Skyla has definitely been looking forward to this, just the same as Red has. “So, what are you going to do to me?”

It is not hard for him to decide on that, since he has spent plenty of time thinking about what he would do if given the chance to have his way with her like this. He gestures for her, showing her what position he wants her to get in as soon as her clothes are off, and the two of them are quick to strip down, so that Skyla can get down on her hands and knees for him.

Red gets into position behind her, and as he rubs his cock against her pussy, he can feel how soaking wet she is, knowing that she is more than ready for this, more than ready for him to take her and to have his way with her. His cock throbs in anticipation just before he pushes into her, filling her entirely with one swift motion, and earning a cry of delight from Skyla, while he moans softly.

In this position, Red is completely in control of everything that they do, and he holds tightly to her hips, increasing his grip the more he gets into it, driven on by his desire, his absolute need for her. Though he has had a lot of fun serving her directly and letting her have her way with him, he can’t deny that, now that he is the one in control, it feels really good to just be able to let loose, and not worry about anything other than what he wants right now.

Jerking his hips forward, he falls into a hectic and selfish pace, not worrying about her for even a second as he takes all that he wants, but Skyla finds herself getting excited by this all the same, loving this side of Red, a side that only makes sense when she considers just how strong of a trainer he is. His submissive side shows his youth and lack of experience, whereas his dominant side shows just how strong he really is, and she adores both sides, glad that she had this chance to experience them both for herself, knowing that this is something she will never forget.

Red does still want to make her come like this, but he is not nearly as intent on trying to hold himself back just for her sake, willing to let things go as far as they will, and seeing to her whenever he can. He just wants to enjoy this as much as possible, to enjoy his victory and claim his prize, and make great use of it until he is so worn out that he can’t keep this up anymore.

Her pussy feels so perfectly tight around his cock, squeezing him like she is ready to milk him dry, and Red keeps pushing himself, closer and closer so that he can fill her right up, and then move right on to what he has in mind next, with no intent of stopping until the very end. The closer he gets, the more frantic his thrusts become, while Skyla is left crying out for him, loving every second that she spends getting pounded by this young trainer, ready to let him use her to his heart’s content.

Finally, once he is no longer able to hold back, the only thing left for him to do is let loose inside of her, completely succumbing to this maddening pleasure. He is so lost in his bliss that he barely even realizes what sort of effect this has on her, but as soon as she feels him unloading inside of her, she is sent into her own orgasm, following right behind him, pushed over the edge by the feeling of his seed. Skyla never realized just how much she loves that feeling before now, but now that she has figured it out, she knows that she could never get enough of that.

It feels so good that she is left to bask in her bliss, while Red takes his time to recover from that, doing what he can to catch his breath and make sure that he is ready for the second round. He wants to keep using her, and already knows what it is that he plans to do next, so as soon as he feels like he is ready to move on, he slowly pulls out of her pussy, making sure that she stays still, in that same pose, while he circles around in front of her. Skyla finds it so easy to understand what he wants, even when he says nothing at all.

Red circles around so that he can stand in front of her, making it clear that he is ready for her to suck him off now, something that Skyla is more than eager to do. He knows that she is good at it from the last time they did something like this, and so he knows that this is going to feel good, looking forward to using her mouth just the same as he has used her pussy. Skyla looks up at him as she moves forward to wrap her lips around his cock, and as soon as he can feel her sucking on his tip, Red lets out a pathetic whimper, feeling his body relax as he gives into her.

This is exactly what he needed next, and for a little while, he decides to just let Skyla set the pace, and show him what she can do, taking her time to please him as she slowly fits him more into her mouth. Once his cock is completely engulfed, then Red is going to take over, and have his way with her, fucking her face until he is satisfied again, and even then, he has a little more in mind for her beyond that.

She fits him in her mouth and starts to gently suck on him at first, taking her time with it while he reaches a hand down to her head, touching her but not pushing her, still letting her stay in control of what she does to him. Red is all riled up again, and it will not be long before he is too caught up in this to even try to hold back with her, but for now, he will let this part last for as long as he can, as Skyla begins rolling her tongue over his cock, doing what she can to get him even more excited for her.

Skyla is happy to be on her knees for him, happy to be the loser in the battle, and to have to show him all that she can do in return as she gives him his prize. This is what she had been looking forward to when she suggested a rematch, and this is what she has been imagining ever since, so glad to find herself in a genuine battle with him, able to see what he was really capable of.

He tightens his grip on the back of her head suddenly, and starts to thrust forward, wanting to use her mouth as much as he can, getting carried away with his lust, unable to hold back at all. Soon enough, he has fallen into an erratic rhythm, thrusting into her mouth, until even this is not enough, and he gets the idea to grab hold of her ponytail. Like this, he is able to pull her hair, yanking her head back and forth as he continues to fuck her face, moaning out, getting a bit louder for her.

Skyla is excited just to hear Red get this loud, the loudest that she has ever heard him, and she is excited to see how rough he can get with her. It is as fun to be dominated by him as it was to dominate him, and she once again counts herself as lucky that she got to experience both of these sides to him, and even luckier that she gets to hear the otherwise quiet boy make so much noise, as he works himself closer and closer to his orgasm, pulling her hair hard as he groans for her and as Skyla lets out gagged moans.

Finally, he lets go, and comes down her throat, pulling hard on her hair as he does. Red is completely overcome by the feeling, lost in that bliss, and does not let go of her the whole time, keeping his tight grip on her ponytail as he comes right down her throat, making her swallow every last bit of it. But Skyla is glad to be able to swallow it all, and moans even more for him to be able to taste it, not letting any of his come go to waste, until he has finally finished. Slowly, he pulls out and releases his hold on her hair, leaving her a bit sore as a result, but that is not something that she is complaining about.

“One more thing,” he says in a quiet voice, the only thing that he has said at all during this encounter. It is easy to forget the sound of his voice, other than his moaning, when that is the only thing that she ever gets to hear from him. But she nods, excited to find out what the other thing is going to be, willing to do whatever he wants all the way until the end.

Red does not say anything else after that, because he shifts his focus to physically showing her what he wants her to do. He has her lay down on her back, so that he can get on top of her, and when she spreads her legs for him, he takes them and pushes them back, pleased to find just how flexible she is in this regard, so that he is able to push her knees back to her ears, making it easy for him to have as much access to her pussy as he needs.

He does not waste any time before thrusting into her this time, filling her all at once with a rough jerk of her hips, making Skyla cry out for him. She really does love this side of him, and how in control he seems to be of everything that he does to her. It only makes her want him that much more, and makes her wish that this never had to end, that she could enjoy getting used and fucked by the young trainer that has her so completely enamored after all the time that they have spent together.

Pushing back on her legs, he pushes as deep into her as he can manage, finding that he can go quite a bit deeper like this, burying his cock in her pussy as he sinks forward. It feels good to do it like this, and he is glad that he thought of doing this position with her, because like this, it is easy for him to thoroughly pound her pussy, completely claiming her as his own. Even if it is just for right now, just for his time traveling in Unova, she is all his, and even if it is just for the time he spends claiming his prize, he can do whatever he wants with her.

“Harder!” she finds herself crying out, unable to resist begging him for more, so desperate to have him use her right up that she has to just moan out for him like that. “Please, fuck me harder!” Her voice comes out so broken and pathetic, making Red feel that much more powerful as he goes to deliver her exactly what she wants, picking up the pace and thrusting into her that much harder, fucking her so that she can be satisfied with it.

All of this is about him, with this being his prize for winning the battle, yet it makes him happy to know just how turned on she is by all of it, and just how much she enjoys when he goes harder and rougher with her, making him want to do even more for her, knowing that it will end up feeling just as good for him. He pounds into her pussy with all that he has, not holding anything back from her as she begs him for more and more, until finally, she is moaning so much that she is not able to speak to keep begging, making it easy for him to assume that he is finally giving her everything that she needs.

He knows that it is more than enough for him, and that he is left overwhelmed with the dizzying pleasure, ready to keep chasing that high, to keep pushing himself closer and closer to his climax, until there is no hope of him holding out anymore, until he has completely worn himself out like this. Until then, he is not going to slow down, showing her just how formidable he can be as a lover, just the same as he is as a trainer. Surely, she is never going to forget just how hard Red could fuck her, or what he could do for her when given the chance.

Skyla is barely hanging on at this point, whimpering and screaming for him, growing so breathless as she is pushed to the edge, and then, there is nothing she can do to stop her orgasm, screaming out for Red as she comes hard. Red continues to pound into her, grunting steadily as he pushes himself to the edge, and he is not far behind her, giving another rough thrust as he lets go, coming hard inside of her, and filling her with seed. He slumps over on top of her then, as he tries to catch his breath.

His visit to Unova has been a big success so far, and he knows that his time with Skyla will be something that he remembers very fondly, as two of the most fun battles that he has had here. At the very least, he knows the aftermath was the best, and he is glad to have made his favorite wager with her twice, so that they could try both things out. Skyla, at the same time, finds herself hoping that this is not the last she sees of Red.

**Author's Note:**

> If you're interested in my writing updates, please follow my fanfiction twitter @WattStalf


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